DE2521816A1 - Artificial sweetening agent - D,L 2-hydroxy 4-methyl valeric acid sodium salt - Google Patents

Artificial sweetening agent - D,L 2-hydroxy 4-methyl valeric acid sodium salt

Info

Publication number
DE2521816A1
DE2521816A1 DE19752521816 DE2521816A DE2521816A1 DE 2521816 A1 DE2521816 A1 DE 2521816A1 DE 19752521816 DE19752521816 DE 19752521816 DE 2521816 A DE2521816 A DE 2521816A DE 2521816 A1 DE2521816 A1 DE 2521816A1
Authority
DE
Germany
Prior art keywords
hydroxy
sodium salt
sweetening
sweetening agent
hmva
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
DE19752521816
Other languages
German (de)
Inventor
Alfred Dr Maierhofer
Hans Dr Wagner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Degussa GmbH filed Critical Degussa GmbH
Priority to DE19752521816 priority Critical patent/DE2521816A1/en
Priority to GB19316/76A priority patent/GB1534957A/en
Priority to FR7614317A priority patent/FR2310991A1/en
Priority to SE7605428A priority patent/SE7605428L/en
Priority to JP51055235A priority patent/JPS51142571A/en
Priority to IT49492/76A priority patent/IT1065983B/en
Priority to CH608276A priority patent/CH600794A5/xx
Priority to US05/687,321 priority patent/US4119738A/en
Publication of DE2521816A1 publication Critical patent/DE2521816A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Seasonings (AREA)

Abstract

Sweetening agent consists of or contains the sodium salt of DL-2-hydroxy-4-methylvaleric acid (Na HMVA). Na HMVA has a sweetening power superior to that of sodium cyclamate, has no aftertaste, and is generally utilisable as a sweetening agent. Since Na HMVA is thermally stable, it can be used for sweetening e.g. warmffoods and baked goods. Aquesou solutions of the salt have been found to be physiologically innocuous. Na HMVA can be used as such for sweetening foods and drinks, or it may be used in admixture with other substances.

Description

Süßstoff Die Erfindung betrifft einen Süßstoff.Sweetener The invention relates to a sweetener.

Es sind zahlreiche chemische Verbindungen bekannt, die süß schmecken. Unter diesen sind jedoch nur wenige, die als Süßstoff in Frage kommen, indem sie einen hohen Süßungswert haben, keinen störenden Nebengeschmack aufweisen, unter den Bedingullgen, unter denen Süßstoffe eingesetzt werden, beständig sind und im Dauergebrauch als physiologisch unbedenklich angesehen werden können.Numerous chemical compounds are known that taste sweet. However, among these are only a few that can be used as a sweetener by using have a high sweetening value, have no annoying aftertaste, under the conditions under which sweeteners are used are stable and im Long-term use can be viewed as physiologically harmless.

Als Süßstoffe werden fast ausschließlich Dulcin, Saccharin, sowie Natriumcyclamat und Calciutncyclamat angewendet (Ullmamls Enzyklopädie der technischen Chemie, Urban und Schwarzenberg, München und Berlin, Band 16, 1965, Seite 478). Von diesen Verbindungen hat sich Dulcin als bedingt toxisch erwiesen (N'aturwissenschaften, 45 (1958), 390). Bs darf daher in einigen Eändern als Süßstoff nicht oder nur begrenzt vertrieben werden.The sweeteners used are almost exclusively dulcin, saccharin, and also Sodium cyclamate and calcium cyclamate applied (Ullmamls encyclopedia of technical Chemie, Urban and Schwarzenberg, Munich and Berlin, Volume 16, 1965, page 478). Of these compounds, dulcin has proven to be of limited toxicity (natural sciences, 45: 390 (1958). In some countries, BS is therefore not allowed as a sweetener or is only allowed to a limited extent to be expelled.

Saccharin und die Cyclamate haben nach neuen Erkenntnissen bei Tieren cancerogene Wirkung gezeigt (Naturwissenschaften 61 (1974), 22). Ihre Anwendung als Süßstoff ist folglich ebenfalls bedenklich.According to new findings, saccharin and the cyclamates have been found in animals shown carcinogenic effects (Naturwissenschaften 61 (1974), 22). Your application as a sweetener is therefore also questionable.

Es ist auch bekannt, l-Alanin-tert.-butylester oder l-Aspartyl-1-phenylalanin-methylester als Süßstoffe einzusetzen (Naturwissenschaften 61 (1974), 22; Chem. Engn. News 52 (1974) 31, 5).It is also known to l-alanine tert-butyl ester or l-aspartyl-1-phenylalanine methyl ester to be used as sweeteners (Naturwissenschaften 61 (1974), 22; Chem. Engn. News 52 (1974) 31, 5).

Diese Verbindungen sind jedoch schwer zugänglich, zudem wenig wärmebeständig und dalier nur begrenzt verwendbar.However, these connections are difficult to access and also have little heat resistance and can only be used to a limited extent.

Es wurde nun gefunden, daß das Natriumsatz der D,L-2-Hydroxy-4-methylvaleriansäure ein Süßstoff ist. Dieses Salz hat einen Süßungswert, der den des Natriumcyclamats übertrifft, es hat keinen Nebengeschmack und ist allgemein als Süßstoff verwendbar. Da es thermisch beständig ist, kann es beispielsweise auch zum Süßen von warmen Speisen und Backwaren verwendet werden. Vorteilhaft ist außerdem, daß es auf einfache Weise aus leicht zugänglichen Substanzen hergestellt werden kann.It has now been found that the sodium set of D, L-2-hydroxy-4-methylvaleric acid is a sweetener. This salt has a sweetening value similar to that of sodium cyclamate surpasses it has has no off-taste and is commonly used as a sweetener usable. Since it is thermally stable, it can also be used as a sweetener, for example Can be used in hot dishes and baked goods. It is also advantageous that it can be easily made from readily available substances.

Wäßrige Lösungen des Salzes sind als Nährlösungen erprobt und gelten als physiologisch unbedenklich.Aqueous solutions of the salt have been tried and tested as nutrient solutions as physiologically harmless.

Der Süßungswert des Natriumsalzes der D,L-2-Hydroxy-4-methylvaleriansäure wird in der nachfolgenden Tabelle mit den Süßungswerten bekannter Süßstoffe verglichen (bestimmt nach Naturwissenschaften 61 (1974), 22; Ann.Eugen. 15 (1949), 24): Süßstoff Schwellwert (mol/Iiter) Sac charo s e 10,4 Natriumcyclamat 0,28 Natriumsalz der D,L-2-Hydroxy-4-methyl-valeriansäure 0,24 Saccharin 0,015 Der hohe Süßungswert des Natriumsalzes der 2-Hydroxy-4-Methylvaleriansäure ist sehr überraschend; denn die Salze ähnlicher 2-Hydroxysäuren, wie beispielsueise der 2-Hydroxyisovaleriansäure, der 2-Hydroxy-3-Methylvaleriansäure, der 2-Hydroxypropionsäure und der 2-Hydroxy-4-methylmercaptobuttersäure, schmecken nicht süß.The sweetening value of the sodium salt of D, L-2-hydroxy-4-methylvaleric acid is compared in the following table with the sweetening values of known sweeteners (determined according to Naturwissenschaften 61 (1974), 22; Ann.Eugen. 15 (1949), 24): Sweetener Threshold value (mol / liter) Saccharo s e 10.4 Sodium cyclamate 0.28 Sodium salt of D, L-2-Hydroxy-4-methyl-valeric acid 0.24 Saccharin 0.015 The high sweetening value of the The sodium salt of 2-hydroxy-4-methylvaleric acid is very surprising; because the Salts of similar 2-hydroxy acids, such as 2-hydroxyisovaleric acid, 2-hydroxy-3-methylvaleric acid, 2-hydroxypropionic acid and 2-hydroxy-4-methylmercaptobutyric acid, don't taste sweet.

Das erfindungsgemäß als Süßstoff zu verwendende Natriumsalz der 2-Hydroxy-4-methylvaleriansäure kann als solches unmittelbar zum Süßen von Speisen und Getränken eingesetzt werden. Gegebenenfalls kommt auch eine Anwendung in Mischung mit anderen Substanzen, Feststoffen oder Flüssigkeiten, in Frage.The sodium salt of 2-hydroxy-4-methylvaleric acid to be used as a sweetener according to the invention As such, it can be used directly to sweeten food and beverages. If necessary, it can also be used in a mixture with other substances, solids or liquids, in question.

Die 2-Hydroxy-4-methylvaleriansäure kann beispielsweise nach einem üblichen Verfahren zur Herstellung von 2-Hydroxysäuren durch Umsetzung von Isovaleraldehyd mit Cyanwasserstoff und Hydrolyse des entstehenden Cyanhydrins mittels Säuren erzeugt werden (Org.Synthesis, Coll. Vol.I, (1941), 336). Das Natriumsalz der Säure kann beispielsweise gewonnen werden, indem eine wäßrige Lösung der Säure mit Natriumhydroxid auf pH 7 eingestellt wird, die Mischung eingedampft wird und der Riickstand in Propanol-(2) umkristallisiert wird. Das auskristallisierende Salz hat die für die Anwendung als Süßstoff erforderliche Reinheit.The 2-hydroxy-4-methylvaleric acid can, for example, after a customary processes for the preparation of 2-hydroxy acids by reacting isovaleraldehyde generated with hydrogen cyanide and hydrolysis of the resulting cyanohydrin by means of acids (Org.Synthesis, Coll. Vol.I, (1941), 336). The sodium salt of the acid can for example, can be obtained by an aqueous solution of the acid with sodium hydroxide is adjusted to pH 7, the mixture is evaporated and the residue in propanol (2) is recrystallized. The crystallizing salt has the for use as Required purity sweetener.

Claims (3)

P a t e n t a n s p r ü c h eP a t e n t a n s p r ü c h e 1. Süßstoff, bestehend aus dem Natriumsalz der D,L-2-Hydroxy-4-methylvaleriansäure.1. Sweetener, consisting of the sodium salt of D, L-2-hydroxy-4-methylvaleric acid. 2. Süßstoff, enthaltend das Natriumsalz der D,L-2-Hydroxy-4 methylvaleriansäure.2. Sweetener containing the sodium salt of D, L-2-hydroxy-4-methylvaleric acid. 3. Verwendung des Natriumsalzes der D,L-2-Hydroxy-4-methylvaleriansäure als Süßstoff. 3. Use of the sodium salt of D, L-2-hydroxy-4-methylvaleric acid as a sweetener.
DE19752521816 1975-05-16 1975-05-16 Artificial sweetening agent - D,L 2-hydroxy 4-methyl valeric acid sodium salt Withdrawn DE2521816A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DE19752521816 DE2521816A1 (en) 1975-05-16 1975-05-16 Artificial sweetening agent - D,L 2-hydroxy 4-methyl valeric acid sodium salt
GB19316/76A GB1534957A (en) 1975-05-16 1976-05-11 Sweeteners
FR7614317A FR2310991A1 (en) 1975-05-16 1976-05-12 SWEETENER
SE7605428A SE7605428L (en) 1975-05-16 1976-05-12 SWEETING AGENT
JP51055235A JPS51142571A (en) 1975-05-16 1976-05-14 Sweetner
IT49492/76A IT1065983B (en) 1975-05-16 1976-05-14 SWEETENING SUBSTANCES
CH608276A CH600794A5 (en) 1975-05-16 1976-05-14
US05/687,321 US4119738A (en) 1975-05-16 1976-05-17 Sweet material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19752521816 DE2521816A1 (en) 1975-05-16 1975-05-16 Artificial sweetening agent - D,L 2-hydroxy 4-methyl valeric acid sodium salt

Publications (1)

Publication Number Publication Date
DE2521816A1 true DE2521816A1 (en) 1976-11-25

Family

ID=5946703

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19752521816 Withdrawn DE2521816A1 (en) 1975-05-16 1975-05-16 Artificial sweetening agent - D,L 2-hydroxy 4-methyl valeric acid sodium salt

Country Status (1)

Country Link
DE (1) DE2521816A1 (en)

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